KR20090037927A - Fat or oil composition - Google Patents

Abstract

A fat or oil composition comprising 100 parts by weight of component (A) consisting of a fat or oil wherein a diacylglycerol in which in constituent fatty acids the content of unsaturated fatty acids is 80 wt.% or higher, the content of conjugated linoleic acid is in the range of 2 to 92 wt.% and the content of i3 unsaturated fatty acids is below 15 wt.% is contained in an amount of 15 wt.% or more, and wherein the content of monoacylglycerol is 5 wt.% or below, the content of free fatty acids is 5 wt.% or below and the weight ratio of 1,3-diacylglycerol/1,2-diacylglycerol is in the range of 1 to 5, and comprising 0.001 to 2 parts by weight of component (B) consisting of tocopherol.

Description

Fat and oil composition {FAT OR OIL COMPOSITION}

The present invention relates to a fat or oil composition having a high content of diacylglycerol containing conjugated linoleic acid.

Against the backdrop of recent health orientation, various studies have been made on the physiological effects of fats and oils. For example, in addition to anti-obesity effect and anti-tumor effect, conjugated linoleic acid has been found to have a therapeutic effect against diabetes and syndrome X (Patent Documents 1 to 5 and Non-Patent Document 1). Application of conjugated linoleic acid having such a function to food has been reported (Patent Document 6).

On the other hand, anti-obesity action etc. are also discovered by diacylglycerol (patent document 7, 8). Moreover, the fats and oils containing diacylglycerol which made specific fatty acids, such as a ω3-type fatty acid and linoleic acid high, are known (patent documents 9-11).

In addition, the oil-fat composition which combined diacylglycerol and a plant sterol has the effect of improving blood cholesterol level, etc. (patent document 12).

Since conjugated linoleic acid is a free fatty acid, it is not suitable for consumption as it is or for use in food due to the unique taste of fatty acids. Thus, attempts to broaden the application range of conjugated linoleic acid have been made by using conjugated linoleic acid as an ester (Patent Documents 13 to 18) and (Non Patent Literatures 2 and 3).

Patent Document 1: International Publication No. 96/06605 Pamphlet

Patent Document 2: International Publication No. 97/46230

Patent Document 3: Japanese Unexamined Patent Publication No. 2003-171272

Patent Document 4: International Publication No. 02/009691 Pamphlet

Patent Document 5: International Publication No. 02/009693 Pamphlet

Patent Document 6: International Publication No. 00/21379 Pamphlet

Patent Document 7: Japanese Patent Application Laid-Open No. 4-300826

Patent Document 8: Japanese Patent Application Laid-Open No. 10-176181

Patent Document 9: International Publication No. 01/109899

Patent Document 10: International Publication No. 02/11552 Pamphlet

Patent Document 11: European Publication No. 0679712

Patent Document 12: International Publication No. 99/48378

Patent Document 13: International Publication No. 00/64854 Pamphlet

Patent Document 14: International Publication No. 04/96748 Pamphlet

Patent Document 15: Japanese Patent Application Laid-Open No. 2003-113396

Patent Document 16: US Patent No. 6432453

Patent Document 17: US Patent No. 6608222

Patent Document 18: European Publication No. 1097708

Non-Patent Document 1: “Lipids”, 1997, Vol. 32, p.853-858

Non Patent Literature 2: “Biotechnology Letters”, 1998, 20, 6, p.617-621

Non Patent Literature 3: “Biotechnol.Prog.”, 2004, 20, p.619-622

Disclosure of the Invention

The present invention provides the following components (A) and (B):

(A) containing 15% by weight or more of diacylglycerol having an unsaturated fatty acid content of at least 80% by weight, a conjugated linoleic acid content of 2 to 92% by weight, and a ω3-based unsaturated fatty acid content of less than 15% by weight, and monoacyl 100 parts by weight of a fat or oil having a glycerol content of 5% by weight or less, a free fatty acid content of 5% by weight or less, and a weight ratio of 1,3-diacylglycerol / 1,2-diacylglycerol of 1 to 5

(B) 0.001 to 2 parts by weight of tocopherol

It is to provide a fat or oil composition containing a.

Detailed description of the invention

In the above-mentioned prior art, the conjugated linoleic acid was not satisfactory in terms of flavor and storage stability even when the conjugated linoleic acid had an increased content of the conjugated linoleic acid. Accordingly, an object of the present invention is to provide an oil-containing composition having a high content of diacylglycerol containing conjugated linoleic acid having a significant anti-obesity effect and excellent stability, and further improving the storage stability of the oil-fat composition.

As a result of the study, the inventors found that the above problems can be solved by adjusting the diacylglycerol content of the fat or oil composition, the conjugated linoleic acid content in the diacylglycerol, the tocopherol content and the like to a specific range. Moreover, it discovered that the obtained fats and oils composition had a feeding inhibitory effect, and came to this invention. Moreover, it was found that the shelf life at low temperature of the obtained oil-fat composition improves.

The fat or oil composition of the present invention contains a fat or oil of the component (A) as an essential component. The fat or oil (A) contains at least 15% by weight of diacylglycerol (hereinafter also referred to simply as "DAG") (hereinafter, simply referred to as "%"), but preferably 15 to 95%, more preferably 20 to 95%, more preferably 35 to 95%, particularly 60 to 90%, most preferably 70 to 85% is preferable in view of the physiological effect, industrial productivity of fats and oils, appearance, food and the like.

In the fat or oil composition of the present invention, the diacylglycerol contained in the fat or oil (A) is 80 to 100% of the constituent fatty acids, but is preferably 85 to 100%, more preferably 90 to 98%, particularly 93 to 98. It is preferable that it is% from an external appearance, a physiological effect, and the industrial productivity of fats and oils. Here, it is preferable that carbon number of unsaturated fatty acid is 14-24, Furthermore, it is 16-22.

In the fat or oil composition of the present invention, the content of conjugated linoleic acid (hereinafter also simply referred to as "CLA") in the fatty acids constituting the diacylglycerol contained in the fat or oil (A) is preferably 2 to 92%, but preferably 5 It is preferable from the viewpoint of lowering body fat, suppressing feeding, preservation, appearance, and intake balance of fatty acids to be 80%, more preferably 15% to 70%, particularly 20% to 60%, and most preferably 25% to 50%.

Conjugated linoleic acid includes 9,11-octadecadienoic acid, 10,12-octadecadienoic acid, their position and geometric isomers, and mixtures thereof. Specifically, cis-9, trans-11-octadecadienoic acid, trans-9, cis-11-octadecadienoic acid, trans-10, cis-12-octadecadiic acid, and the like. As a method for producing conjugated linoleic acid, for example, a fat or oil containing linoleic acid or a linoleic acid may be used as a raw material, and biochemical conjugation using enzymes of ruminants or microorganisms, or chemical conjugation by heating under alkaline conditions.

In the aspect of the present invention, in the fatty acids constituting the diacylglycerol contained in the fat or oil (A), the content of oleic acid is preferably 1 to 65%, further 2 to 50%, particularly 5 to 40%, most preferably Preferably it is 10 to 30% in terms of preservation, appearance, and intake balance of fatty acids. Moreover, it is preferable that content of the dioleyl glycerol in diacyl glycerol is less than 45% in particular from an external appearance and a physiological effect from 0 to 40%.

In the fat or oil composition of the present invention, in the fatty acids constituting the diacylglycerol contained in the fat or oil (A), the content of the ω3-unsaturated fatty acid is less than 15%. It is preferable in terms of balance. As an omega-3 unsaturated fatty acid, (alpha)-linolenic acid, eicosapentaenoic acid, docosahexaenoic acid, etc. are mentioned, for example.

In the oil-fat composition of this invention, in the fatty acid which comprises the diacylglycerol contained in fats and oils (A), content of saturated fatty acid is less than 20%, Preferably it is 0-10%, Furthermore, 1-7%, Especially 2 It is-7%, Most preferably, it is 2-6%, It is preferable at the point of appearance, the physiological effect, and industrial productivity of an oil-fat. As saturated fatty acid, C14-C24, especially 16-22 thing are preferable, and palmitic acid and stearic acid are more preferable.

In the aspect of this invention, it is preferable that content of trans unsaturated fatty acids other than conjugated linoleic acid is 0 to 3.5% among fatty acids which comprise the diacylglycerol contained in fats and oils (A), It is especially flavor that it is 0.1 to 3% It is preferable from the viewpoint of the physiological effect, appearance, preservation, and industrial productivity of fats and oils.

In the aspect of this invention, it is preferable that content of a C12 or less fatty acid is 5% or less from a fatty acid among the fatty acids which comprise the diacylglycerol contained in fats and oils (A), Furthermore, 0-2%, Especially 0- It is preferable that it does not contain 1% most preferably substantially. The residual constituent fatty acids are preferably 14 to 24 carbon atoms, particularly 16 to 22 carbon atoms.

In the aspect of this invention, it is preferable that the ratio of 1, 3- diacyl glycerol (1, 3-DAG) in the diacyl glycerol (DAG) contained in fats and oils (A) is 50% or more, More preferably, 52 It is preferable from the viewpoint of physiological effect, preservation, industrial productivity and flavor of fats and oils which are -100%, 54-90%, especially 56-80%. Here, DAG consists of 1, 3-DAG and 1,2- diacylglycerol (1, 2-DAG). Precisely 2,3-diacylglycerol is present, but in the present invention, it will be treated as 1,2-DAG.

In the present invention, the weight ratio of 1,3-DAG / 1,2-DAG in fats and oils is 1 to 5, but preferably 1.5 to 3.8, more preferably 2 to 3.5, particularly 2.1 to 3.2, storage stability and physiology at low temperature. It is preferable at the point of effect and industrial productivity of fats and oils.

In the aspect of the present invention, the oil or fat (A) preferably contains 4.9 to 84.9% of triacylglycerol (hereinafter also referred to simply as "TAG"), more preferably 4.9 to 64.9%, and further 6.9 to 39.9. %, Especially 6.9-29.9%, Most preferably, it contains 9.8-19.8% is preferable from a physiological effect, the industrial productivity of fats and oils, and an external appearance.

In the aspect of the present invention, the content of the conjugated linoleic acid is preferably 50% or less, more preferably 1 to 35%, particularly 2 to 20%, most preferably in the constituent fatty acid of the triacylglycerol contained in the fat or oil (A). It is preferable that it is 5 to 15% from a viewpoint of storage property, a physiological effect, and the industrial productivity of an oil-fat.

In the aspect of this invention, the weight ratio ((1) Formula) of content of the conjugated linoleic acid in the fatty acid which comprises the diacylglycerol contained in fats and oils (A), and content of the conjugated linoleic acid in the fatty acid which comprises triacylglycerol is 1 It is preferable that it is -10, Furthermore, it is 2-9, especially 3-8, Most preferably, it is preferable from a viewpoint of preservation | preservation and physiological effect.

CLA content in DAG / CLA content in TAG... (1) expression

In the aspect of this invention, it is preferable that content of oleic acid is 15-70% in the constituent fatty acid of the triacylglycerol contained in fats and oils (A), Furthermore, 20-65%, Especially 30-60%, Most preferably It is preferable that it is 45 to 55% from a viewpoint of storage property, a physiological effect, and the industrial productivity of fats and oils.

In the aspect of this invention, it is preferable that the constituent fatty acid of the triacylglycerol contained in fats and oils (A) is 70-100% of unsaturated fatty acids, More preferably, it is 80-100%, Furthermore, 90-100%, Especially 93 It is preferable from the viewpoint of the physiological effect and the industrial productivity of fats and oils which are-98%, Most preferably, 94-98%. Carbon number of unsaturated fatty acid is 10-24, Furthermore, it is preferable that it is 16-22 from a viewpoint of a physiological effect and the industrial productivity of fats and oils.

In the fat or oil composition of the present invention, the fat or oil (A) contains 5% or less of monoacylglycerol (hereinafter also referred to simply as "MAG"), but is preferably 0.1 to 5%, more preferably 0.1 to 2%. %, Furthermore, it is preferable to contain 0.1 to 1.5%, especially 0.1 to 1.3%, most preferably 0.2 to 1% from the viewpoint of flavor, appearance, fuming, industrial productivity of fats and oils, application to food, etc.

In the aspect of the present invention, the constituent fatty acid of the monoacylglycerol contained in the fat or oil (A) is preferably the same constituent fatty acid as the diacylglycerol in view of the physiological effect and the industrial productivity of the fat or oil.

In the fat or oil composition of the present invention, the content of the free fatty acid and / or salt (hereinafter also simply referred to as "FFA") contained in the fat or oil (A) is 5% or less, but preferably 0 to 3.5%, furthermore 0 to 2%, especially 0.01 to 1%, and most preferably 0.05 to 0.5% are preferred in terms of flavor, fuming, work comfort during cooking, and industrial productivity of fats and oils.

In the aspect of the present invention, in all of the fatty acids constituting the fat or oil (A), the content of the unsaturated fatty acid is preferably 80 to 100%, more preferably 85 to 100%, particularly 90 to 100%, most preferably 93 to It is preferable that it is 98% from a physiological effect and the industrial productivity of fats and oils.

In the aspect of the present invention, in the total fatty acids constituting the fat or oil (A), the content of fatty acids having four or more carbon-carbon double bonds is selected from the group consisting of oxidative stability, work comfort at cooking, physiological effect, coloring, flavor, and the like. From the viewpoint of 0 to 40%, preferably 0 to 20%, more preferably 0 to 10%, particularly 0 to 1%, most preferably substantially free.

In the aspect of this invention, it is preferable that content of trans unsaturated fatty acid is 0 to 4% among all the fatty acids which comprise fats and oils (A), and furthermore, it is 0.1 to 3.5%, and it is the industry of flavor, a physiological effect, an appearance, fats and oils It is preferable at the point of productive productivity.

In this invention, content of trans unsaturated fatty acid is the value measured by AOCS method (American Oil Chem. Soc. 0fficial Method: Celf-96, 2002).

In the aspect of this invention, it is preferable that content of conjugated linoleic acid is 2-92% among all the fatty acids which comprise fats and oils (A), Furthermore, 5-65%, Especially 10-50%, Most preferably, 15- It is preferable that it is 30% from the viewpoint of the physiological effect, storage property, application to food, and the industrial productivity of fats and oils.

In the aspect of the present invention, in all of the fatty acids constituting the fat or oil (A), the content of oleic acid is preferably 20 to 65%, more preferably 25 to 60%, particularly 30 to 55%, and most preferably 35 to 50 It is preferable that it is% from a viewpoint of storage property, the application to food, etc., and the industrial productivity of fats and oils.

In the aspect of this invention, it is preferable that content of linolenic acid is 15% or less in all the fatty acids which comprise fats and oils (A), Furthermore, it is 0.1 to 12%, Especially 1 to 10%, Most preferably, it is 2 to 8% It is preferable from the viewpoint of preservation, application to food, etc., industrial productivity of fats and oils, and physiological effects.

In the aspect of the present invention, any of vegetable and animal fats and oils may be used as the raw material of the fat or oil (A). As a specific raw material, rapeseed oil, sunflower oil, corn oil, soybean oil, rice bran oil, safflower oil, cottonseed oil, tallow, etc. are mentioned, for example. In addition, those obtained by fractionating and mixing these fats and oils and adjusting fatty acid compositions by hydrogenation or transesterification can be used as raw materials, but those without hydrogenation reduce the trans acid content in all fatty acids constituting the fat or oil composition. It is preferable at the point to make it.

In addition, as a fats and oils which become a raw material of fats and oils (A), besides deodorization oil, undeodorized fats and oils which are not deodorized previously can be used. In the aspect of the present invention, the use of undeodorized fats and oils in part or all of the raw materials can reduce transunsaturated fatty acids other than conjugated linoleic acid and can leave plant sterols, plant sterol fatty acid esters and tocopherols derived from the raw material fats and oils. desirable.

In the aspect of the present invention, the fat or oil (A) can be obtained by the above-mentioned conjugated linoleic acid, esterification reaction of fatty acid and glycerin derived from fat or oil, transesterification reaction of fats and oils containing conjugated linoleic acid, and glycerin. Excess monoacylglycerol produced by the reaction can be removed by molecular distillation or chromatography. These reactions can also be carried out by chemical reaction using an alkali catalyst or the like. However, it is preferable to perform the reaction under enzymatically mild conditions using 1,3-position selective lipase and the like in terms of flavor and the like. In particular, it is preferable from the viewpoint of flavor and preservation that dilution by plant fat or oil of the conjugated linoleic acid high content diacylglycerol, or transesterification reaction of conjugated linoleic acid high content diacylglycerol with a plant fat or oil is carried out.

The oil-fat composition of this invention needs to contain the tocopherol of component (B). Although content of tocopherol (B) is 0.001-2 parts with respect to 100 weight part of fats and oils (A) (henceforth simply "part") from a viewpoint of flavor, oxidation stability, coloring, etc., it is preferable that it is 0.005-1.5 denier. Furthermore, 0.01-1 part, especially 0.01-0.5 part, and 0.02-0.2 denier are most preferable.

In the aspect of the present invention, as tocopherol (B), α, β, γ, δ-tocopherol or a mixture thereof can be used. Among them, it is preferable to use δ-tocopherol from the viewpoint of oxidative stability. In particular, when the fat or oil composition of the present invention is mixed with water or used in foods containing water, when stored for a long time or in a bright place, the use of δ-tocopherol prevents flavor deterioration and unusual taste. It is preferable at the point.

As a commercial item of tocopherol, for example, Emix D, Emix 80 (Aizai Co., Ltd.)

, MDE-6000 (Yashiro Co., Ltd.), E oil-400 (Riken Vitamin Co., Ltd.), etc. are mentioned.

In the aspect of the present invention, an antioxidant may be added to the fat or oil composition in addition to the tocopherol (B). As an antioxidant, what may be normally used as long as it is used for food. For example, butylhydroxytoluene (BHT), butylhydroxyanisole (BHA), t-butylhydroquinone (TBHQ), catechin, vitamin C or derivatives thereof, phosphorus fat, rosemary extract, and the like, may be mentioned. Preference is given to using vitamin C or derivatives thereof, catechins, and rosemary extracts, particularly preferably at least one mixture thereof.

As vitamin C or its derivatives, it is preferable to dissolve in fats and oils (A), higher fatty acid esters of vitamin C, for example, fatty acid esters having 12 to 22 carbon atoms of acyl groups, and L-ascorbic acid palmi Tate, L-ascorbic acid stearate are particularly preferred, and L-ascorbic acid palmitate is most preferred.

In the aspect of the present invention, the content of vitamin C or derivatives thereof is preferably 0.004 to 0.1 denier ascorbic acid, more preferably 0.006 to 0.08 part, particularly 0.008 to 0.06 denier with respect to 100 parts of fats and oils (A).

In the embodiment of the present invention, when the fat or oil composition is mixed with water or used in foods containing water, and when stored for a long time or bright place, L-ascorbic acid fatty acid ester is substantially used as an antioxidant. It is preferable that it is not contained in the point which prevents flavor deterioration and unusual taste generation.

In the aspect of the present invention, the fat or oil composition preferably contains plant sterols of component (C). The plant sterols in the present specification are not limited to those in which the hydroxyl group does not ester bond with a fatty acid and is free (free), but also contains derivatives such as ester.

In the aspect of this invention, it is preferable that content of plant sterols (C) is 0.05-30 denier with respect to 100 parts of fats and oils (A), More preferably, it is 0.3-20 parts, Furthermore, 1-10 parts, Especially 2- 8 parts, most preferably 2.5 to 4.7 parts is preferable in view of cholesterol lowering action, flavor, appearance, low temperature storage property and industrial productivity of fats and oils. Here, when containing derivatives, such as an ester body, as a component (C), the value converted into the free body is made into content of a component (C).

In an aspect of the present invention, plant sterols (C) also include plant stanols. As plant sterols, for example, brassicasterol, isofucosterol, stigmasterol, 7-stigmagsterol, α-sitosterol, β-cytosterol, camphorsterol, brassicastanol, isofucostanol, stigmastanol, Free bodies such as 7-stigmastanol, α-cytostanol, β-cytostanol, campestanol, cycloartenol, cholesterol, avenasterol, and esters such as fatty acid esters, ferulic acid esters, and cinnamic acid esters Sieve. Among these plant sterols, brassicasterol, camphorsterol, stigmasterol and β-sitosterol are preferable in terms of industrial productivity and flavor of fats and oils.

In the aspect of the present invention, the total content of brassicasterol, camphorsterol, stigmasterol, and β-sitosterol in the plant sterols (C) is preferably 90% or more, more preferably 92 to 100%, particularly 94 to 99%. It is preferable in terms of flavor, appearance, industrial productivity of fats and oils, crystal precipitation, shelf life at low temperature, and physiological effect.

The content of brassicasterol in the plant sterols (C) is preferably 0.5 to 8%, more preferably 1 to 7.5%, particularly 3 to 7% at flavor, appearance, industrial productivity of fats and oils, crystal precipitation and low temperature. It is preferable at the point of preservation and physiological effect.

The content of camphorsterol in the plant sterols (C) is preferably 10 to 40%, more preferably 15 to 35%, particularly 22 to 30%, in terms of flavor, appearance, industrial productivity of fats and oils, crystal precipitation, and low temperature. It is preferable in terms of preservation and physiological effects.

It is preferable that content of the stigmasterol in plant sterols (C) is 3 to 30%, Furthermore, it is 5 to 25%, Especially 7 to 15% is industrial flavor of flavor, appearance, fats and oils, crystal precipitation, and low temperature It is preferable in terms of preservation and physiological effects.

It is preferable that content of (beta) -sitosterol in plant sterols (C) is 30 to 60%, Furthermore, it is 35 to 58%, especially 40 to 56% in flavor, appearance, the industrial productivity of fats and oils, crystal precipitation, and low temperature. It is preferable at the point of preservation and physiological effect.

It is preferable that content of cholesterol in plant sterols (C) is 1% or less, Furthermore, it is 0.01 to 0.8%, Especially 0.1 to 0.7%, Most preferably, 0.2 to 0.6% The industrial productivity of blood cholesterol lowering and fats and oils Preferred at

In the aspect of the present invention, when the plant sterol fatty acid ester is contained in the plant sterols (C), the content of the unsaturated fatty acid in the constituent fatty acids is preferably 80% or more, more preferably 85 to 100%, particularly 86 to 98%. Most preferably, it is 88-93% from a viewpoint of flavor, an external appearance, storage property at low temperature, crystal precipitation, the industrial productivity of an oil-fat, oxidative stability, and a physiological effect.

In the aspect of the present invention, it is preferable that the weight ratio (CLA / PS) of the CLA content in the DAG to the content of the plant sterols (hereinafter also referred to simply as "PS") in the fats and oils is preferably less than 700, more preferably 1 It is preferable from the viewpoint of preservation at low temperature to -400, 5 to 250, especially 10 to 100, and most preferably 15 to 70. It is preferable to apply this to the case where the weight ratio of 1,3-DAG / 1,2-DAG in fats and oils is 1.5-3.8, Furthermore, it is 2-3.5, especially 2.1-3.2 It is the thing of the preservation at low temperature, a physiological effect, fats and oils It is preferable at the point of industrial productivity. In addition, when a plant sterol contains derivatives, such as a plant sterol fatty acid ester (henceforth simply a "PSE", etc.), these are converted into a free body, and CLA / PS value is calculated | required by making the total weight into "PS".

In an aspect of the present invention, the fat or oil composition preferably further contains a crystal inhibitor (D). Examples of the crystal inhibitor include polyol fatty acid esters such as polyglycerol condensed ricinoleic acid ester, polyglycerin fatty acid ester, sucrose fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, and propylene glycol fatty acid ester. Polyglycerol fatty acid esters, sucrose fatty acid esters, sorbitan fatty acid esters are preferred, and polyglycerol fatty acid esters are particularly preferred. Moreover, it is preferable that the value calculated by HLB fine Griffin formula (J. Soc. Cosmet. Chem., 1,311 (1949)) of a polyol fatty acid ester is 4 or less, especially 0.1-3.5.

In the aspect of the present invention, in the case where the polyglycerol fatty acid ester is used as the crystal inhibitor (D) in the fat or oil composition, the content of the unsaturated fatty acid in the fatty acids constituting the polyglycerol fatty acid ester is preferably 50 to 95%, furthermore It is preferable that it is 51 to 80%, especially 52 to 60% from a viewpoint of crystal suppression, solubility to fats and oils, and oxidation stability. Moreover, it is preferable to make content of unsaturated fatty acid into 50% or more from the point which makes melting of the polyglycerol fatty acid ester easy to fats and oils. In addition, from the point of suppressing the crystallization of fats and oils, it is preferable to make content of unsaturated fatty acid into 95% or less. It is preferable that carbon number of the unsaturated fatty acid which comprises polyglycerol fatty acid ester is 10-24, and it is preferable that it is 16-22 further. Specifically, palmitoleic acid, oleic acid, petroleum acid, oleic acid, linoleic acid, linolenic acid, gadolenic acid, erucic acid, etc. are mentioned, and oleic acid, linoleic acid, and gadolenic acid are preferable. In the unsaturated fatty acid which comprises polyglycerol fatty acid ester, it is preferable that content of oleic acid is 80% or more, Furthermore, it is preferable that it is 90 to 99.8% in terms of crystal suppression, solubility to fats and oils, cost, oxidative stability, and flavor. Among the unsaturated fatty acids constituting the polyglycerol fatty acid ester, the content of linoleic acid is preferably 10% or less, and more preferably 0.1 to 5% in terms of crystal inhibition, solubility for oils and fats, cost, oxidative stability, and flavor. Among the unsaturated fatty acids constituting the polyglycerol fatty acid ester, the content of gadolenic acid is preferably 10% or less, and particularly preferably 0.1 to 5% in terms of crystallization inhibition, solubility for fats and oils, cost, oxidative stability, and flavor.

In the aspect of the present invention, in the case where the polyglycerol fatty acid ester is used as the crystal inhibitor (D) in the fat or oil composition, the content of the saturated fatty acid in the fatty acids constituting the polyglycerol fatty acid ester is preferably 5 to 50%. It is preferable that it is 20 to 49%, especially 40 to 48% from a viewpoint of crystal suppression, solubility to fats and oils, and oxidation stability. It is preferable that carbon number of this saturated fatty acid is 10-24, Furthermore, it is 12-22. Specifically, lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, etc. are mentioned, and myristic acid, palmitic acid, and stearic acid are preferable. It is preferable that content of palmitic acid is 80% or more among the saturated fatty acids which comprise a polyglycerol fatty acid ester, and it is especially preferable that it is 90 to 99.8% in terms of crystal suppression, solubility to fats and oils, cost, oxidative stability, and flavor. Constitution of Polyglycerol Fatty Acid Esters Among the saturated fatty acids, the content of myristic acid is preferably 10% or less, and particularly preferably 0.1 to 5% in terms of crystallization inhibition, solubility for oils and fats, cost, oxidation stability, and flavor. Constitution of Polyglycerol Fatty Acid Esters Among the saturated fatty acids, the content of stearic acid is preferably 10% or less, and particularly preferably 0.1 to 5% in terms of crystallization suppression, solubility for fats and oils, cost, oxidative stability, and flavor.

In the aspect of the present invention, the content of the crystal inhibitor (D) is 0.01 to 2 parts with respect to 100 parts of fats and oils (A), further 0.02 to 0.5 parts, especially 0.05 to 0.2 denier solubility in oils, costs, flavors, crystals It is preferable at the point of suppression.

In the aspect of this invention, it is preferable that an oil-fat composition further contains C2-C8 organic carboxylic acid and / or its salt. It is preferable that content of C2-C8 organic carboxylic acid is 0.001-0.01 denier with respect to 100 parts of fats and oils (A), Furthermore, 0.0012-0.007 part, Especially 0.0015-0.0045 part, Most preferably, 0.0025-0.0034 denier It is preferable in terms of appearance, oxidation stability. As the organic carboxylic acid, citric acid is preferable.

In an aspect of the present invention, the fat or oil composition selects a raw material fat and oil and a manufacturing method so that the component (A) of the composition is in a predetermined ratio, adds the component (B) to it, and further, the component (C) as necessary. ), Component (D), antioxidant, organic carboxylic acid and / or its salt, etc. can be added, and it can obtain by heating and stirring suitably.

Since the oil-fat composition of this invention is excellent in the point of storage property, a flavor, a texture, an appearance, work comfort at the time of cooking, a physiological effect, etc., it can apply to various foodstuffs.

Examples of the food to which the fat or oil composition of the present invention is applied include processed fats and oils containing the fat or oil composition as part of the food. As such a fat-and-oil processed food, the health food, a functional food, a specific health food, etc. which exhibit a specific function and aim at health improvement are mentioned, for example. Specific products include bakery foods such as breads, cakes, biscuits, pies, pizza crusts and bakery mixes, oil-in-water emulsions such as soups, sauces, dressings, mayonnaise, coffee whiteners, ice creams and whip creams, margarine, spreads and butter creams. Water-in-oil emulsions, snacks such as potato chips, snacks such as chocolate, caramel, candy, desserts, meat processed foods such as ham, sausages, hamburgers, dairy products such as milk, cheese, yogurt, dough, en rover, Peeling fats and oils, cotton, frozen food, retort food, a drink, roux, etc. are mentioned. In addition to the oil-fat composition of this invention, it can manufacture by adding the food raw material generally used according to the kind of oil-processed food. Although the compounding quantity with respect to the foodstuff of the oil-fat composition of this invention changes also with kinds of foodstuff, generally 0.1-100%, especially 1-80% are preferable.

Moreover, the oil-fat composition of this invention can be used as food raw materials, such as cooking oil used for frying or roasting. In particular, side dishes such as croquettes, tempura, pork cutlet, tempura, fried fish, and spring rolls, snacks such as potato chips, tortilla chips, and fabric potatoes, fried cookies such as fried senbei, fried potatoes, fried chicken, donuts, It is suitable for cooking instant noodles.

In addition, when manufacturing a food using the fats and oils composition of this invention, when the fats and oils derived from a food raw material are contained, the weight ratio of the fats and oils derived from a food raw material to the fats and oils composition of this invention is the fats and oils derived from a food raw material / this invention. It is preferable that the oil-fat composition of is 95/5-1/99, Furthermore, it is preferable that it is 95/5-5/95, Especially 85/15-5/95, Most preferably, it is 40/60-5/95.

The oil-fat composition of this invention can be used for an oil-in-water emulsion. The weight ratio of the oil phase and the water phase is preferably 1/99 to 90/10, and more preferably 10/90 to 80/20, particularly 30/70 to 75/25. When using the oil-fat composition of this invention for an oil-in-water emulsion, it is preferable to contain 0.01 to 5%, especially 0.05 to 3% of an emulsifier. Examples of emulsifiers include egg proteins, soy proteins, milk proteins, proteins isolated from these proteins, various proteins such as (partial) degradation products of these proteins, sucrose fatty acid esters, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, Glycerin fatty acid monoesters, polyglycerol fatty acid esters, polyglycerol condensed ricinoleic acid esters, glycerin organic acid fatty acid esters, propylene glycol fatty acid esters, lecithin or enzyme degradation products thereof. When using the oil-fat composition of this invention for an oil-in-water emulsion, it is preferable to contain 0 to 5%, especially 0.01 to 2% of a stabilizer. Examples of the stabilizer include thickened polysaccharides and starches such as xanthan gum, gellan gum, guar gum, carrageenan, pectin, tragant gum and glucomannan. Moreover, according to the kind of food, seasonings, such as salt, sugar, vinegar, fruit juice, and seasoning, fragrances, such as a spice and a flavor, coloring, a preservative, antioxidant, etc. can be used suitably. Using these raw materials, oil-in-water fat-containing foods, such as mayonnaise, dressing, coffee whitener, ice cream, whipped cream, and beverage, can be manufactured by conventional methods.

The oil-fat composition of this invention can be used for a water-in-oil type emulsion. The weight ratio of the water phase and the oil phase is preferably 85/15 to 1/99, and more preferably 80/20 to 10/90, particularly 70/30 to 35/65. When the oil-fat composition of this invention is used for a water-in-oil type emulsion, it is preferable to contain an emulsifier 0.01-5%, especially 0.05-3%. Examples of emulsifiers include egg proteins, soy proteins, milk proteins, proteins isolated from these proteins, various proteins such as (partial) decomposition products of these proteins, sucrose fatty acid esters, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, glycerin Fatty acid monoesters, polyglycerin fatty acid esters, polyglycerol condensed ricinoleic acid esters, glycerin organic acid fatty acid esters, propylene glycol fatty acid esters, lecithin or enzyme degradants thereof. In addition, depending on the type of food, seasonings such as salt, sugar, vinegar, fruit juice, seasonings, spices such as spice and flavor, stabilizers such as thick polysaccharides and starch, coloring agents, preservatives, antioxidants, and the like can be used. have. These raw materials can be used to prepare water-in-oil fat-containing oil-containing foods such as margarine, spreads and butter cream by conventional methods.

The fat or oil composition of the present invention has excellent physiology such as body fat accumulation inhibitory effect, visceral fat accumulation inhibitory effect, weight gain inhibitory effect, serum triglyceride increase inhibitory effect, insulin resistance improvement effect, blood sugar level suppression effect, HOMA index improvement effect, feeding inhibition effect, etc. Have activity. Because of these excellent properties, the fat or oil composition of the present invention can be used in certain health foods, food for the sick, health functional small foods, and pharmaceuticals.

In addition, the fat or oil composition of the present invention can be used for pharmaceuticals in the form of capsules, tablets, granules, powders, solutions, gels and the like. In addition to the fat or oil composition, in addition to the fat or oil composition, excipients, disintegrants, binders, lubricants, surfactants, alcohols, water, water-soluble polymers, sweeteners, scavengers, acidulants and the like which are generally used may be added. It can manufacture. Although the compounding quantity with respect to the pharmaceutical product of the oil-fat composition of this invention differs also according to the use and form of a pharmaceutical product, it is generally 0.1 to 80%, Furthermore, it is preferable that it is 0.2 to 50%, especially 0.5 to 30%. In addition, the dosage is preferably administered by dividing 0.2-50 g into 1 to several times per day as an oil-fat composition. The administration period is preferably 1 month or more, 2 months or more, and 3 months to 12 months.

The fat or oil composition of the present invention can be used for feed. As feed, for example, for livestock feed for cattle, pigs, chickens, sheep, horses, goats, etc., for small animals for rabbits, rats, mice, etc., for eel, sea bream, sea bream, shrimp, etc. Pet food used for feed, dogs, cats, small birds, squirrels, and the like. Although the compounding quantity with respect to the feed of the fats and oils composition of this invention differs also according to the use of a feed, etc., generally 1-30%, especially 1-20% are preferable. The compounding is performed by replacing all or part of the fat or oil in the feed with the fat or oil composition of the present invention.

The feed is prepared by mixing feed materials generally used, such as meat, protein, grains, rice bran, fork, saccharides, vegetables, vitamins, and minerals, as appropriate, in addition to the fat or oil composition.

As the meat, for example, meat, meat and its by-products, processed products (rendered products of the raw materials such as meatballs, meatball mills and chicken mills) such as cattle, pigs, sheep (merton or lamb), rabbits and kangaroos, Fish and shellfish such as tuna, bonito, horse mackerel, sardines, scallops, seashells, and fish meal (fish mill) may be mentioned. Examples of the protein include milk proteins such as casein and wei, animal proteins such as egg protein and plant proteins such as soy protein. As grains, wheat, barley, rye, milo, corn, etc. are mentioned, for example. As rice bran, rice bran, bran, etc. are mentioned, for example. Examples of forklifts include soybean jelly. It is preferable that the total amount of meat, protein, grains, rice bran and fork rice in the feed is 5 to 93.9%.

Examples of the saccharides include glucose, oligosaccharides, sugar, molasses, starch, liquid sugar, and the like, and those containing 5 to 80% in the feed are preferable. As vegetables, vegetable extract etc. are mentioned, for example, It is preferable to contain 1-30% in feed. Vitamins include, for example, A, B _1, B _2, D, E, there may be mentioned niacin, pantothenic acid, carotene, etc., it is preferable to contain 0.05 to 10 percent of feed. As minerals, calcium, phosphorus, sodium, potassium, iron, magnesium, zinc, etc. are mentioned, for example, It is preferable to contain 0.05-10% in feed. In addition, a gelling agent, a prosthetic agent, a pH adjuster, a seasoning, a preservative, a nutrient reinforcing agent or the like, which are generally used in a feed, may be contained as necessary.

Example 1 Preparation of Oils and Fats

(1) Preparation of conjugated linoleic acid (CLA)

After mixing 1050g of propylene glycol and 350g of potassium hydroxide, it heated up to 60 degreeC, stirring, and dissolved potassium hydroxide completely. Thereafter, nitrogen bubbling was performed at 60 ° C. for 30 minutes to remove dissolved oxygen. Then, this was heated up to 130 degreeC and 700 g of linoleic acid (made by Tokyo Chemical) was added little by little. It heated up to 157 degreeC under nitrogen atmosphere, stirred for 4 hours, and performed the conjugation reaction. After cooling this to room temperature, 1 L of 5N hydrochloric acid was added, and pH was adjusted to 3. Hexane was added to the reaction product, solvent extraction was performed, the solvent was distilled off with the evaporator, and CLA 700g was obtained.

(2) Preparation of Fats and Oils A

1100 parts of CLA prepared in (1) and 110 parts of immobilized lipase were mixed and heated to 40 ° C. under a nitrogen atmosphere. Subsequently, 180.5 parts of glycerin were added, and esterification reaction was performed at 40 degreeC under reduced pressure (2-5 torr) for 7 hours. After filtration to remove the immobilized enzyme, the reaction product (TAG 5.7%, DAG 73.2%, MAG 12.8%, FFA 8.3%) was charged into silica gel column chromatography (Wako C-200, manufactured by Wako Pure Chemical Industries), Elution with an organic solvent gave purification. Hexane, hexane-ethyl acetate (97: 3, V / V), hexane-ethyl acetate (9: 1, V / V), hexane-ethyl acetate (4: 1, V / V), hexane-ethyl acetate (3: 1, V / V) and hexane-ethyl acetate (2.5: 1, V / V) were eluted sequentially, and the DG fraction was obtained. To 100 parts of fats and oils obtained by distilling a solvent off with the evaporator, what added 0.02 parts of tocopherols (mixed tocopherols MDE-6000 made from Yashi) was made into fats and oils A. The glyceride composition and fatty acid composition are shown in Table 1. Moreover, the 1, 3-DAG content of fats and oils A was 78.7%, and the 1, 2-DAG content was 19.7%. Thus, 1,3-DAG / 1,2-DAG = 4 (weight ratio).

(3) Preparation of Oil B

520 parts of CLA and 52 parts of immobilized lipase which were prepared in (1) were mixed, and it heated at 40 degreeC by nitrogen atmosphere. Subsequently, 56.9 parts of glycerin were added, and esterification reaction was performed at 50 degreeC under reduced pressure (2-5 torr) for 20 hours. After filtration to remove the immobilized enzyme, the reaction product (TAG 41.8%, DAG 36.8%, MAG 1.2%, FFA 20.2%) was charged into silica gel column chromatography (Wako C-200, manufactured by Wako Pure Chemical Industries), Elution with organic solvent (hexane-ethyl acetate (97: 3, V / V)) removed the DG fraction and the MG fraction. This was further purified by Florisil column chromatography. That is, after eluting a TG fraction with hexane and hexane-ethyl acetate (30: 1, V / V), the solvent was distilled off with the evaporator. To 100 parts of the obtained fats and oils, what added 0.02 parts of tocopherols (mixed tocopherols MDE-6000, the product made by Yashi) was made into fats and oils B. The glyceride composition and fatty acid composition are shown in Table 1.

(4) Preparation of fats and oils C

400 parts of fish oil (manufactured by Cao) and 16 parts of glycerin were mixed, and transesterification reaction was performed at 100 ° C. for 4 hours under reduced pressure (0.133 kPa) in the presence of 1.2 parts of sodium methylate. The obtained reaction product was refine | purified by silica gel chromatography similarly to (2), and the solvent was distilled off with the evaporator. Subsequently, 0.02 part of tocopherol (mixed tocopherol MDE-6000, the product made by Yashi) was added with respect to 100 parts of fats and oils obtained, and the fats and oils C were obtained. The glyceride composition and fatty acid composition are shown in Table 1.

(5) Preparation of maintenance D

400 parts of heavy chain fatty acid triglycerides (Coconade MT, manufactured by Cao) and 16 parts of glycerin were mixed, and 1.2 parts of sodium methylate was subjected to a transesterification reaction at 100 ° C. for 4 hours under reduced pressure (0.133 kPa). The obtained reaction product was purified by silica gel chromatography in the same manner as in (2), and the solvent was distilled off with an evaporator. Next, 0.02 parts of tocopherol (mixed tocopherol MDE-6000, manufactured by Yashi) was added to 100 parts of the obtained fats and oils to obtain fats and oils D. The glyceride composition and fatty acid composition are shown in Table 1.

(6) Preparation of Maintenance E

75 parts of potassium hydroxide were melt | dissolved completely in 225 parts of propylene glycol, nitrogen bubbled for 20 minutes, and it heated up to 120 degreeC under nitrogen atmosphere. Subsequently, after 180 parts of safflower oils were dripped, reaction was performed at 170 degreeC for 2.5 hours. 300 parts of the obtained reaction products and 12 parts of glycerin were subjected to transesterification reaction at 100 ° C for 4 hours under reduced pressure (0.133 kPa) in the presence of 0.8 parts of sodium methylate. This was fractionated by silica gel chromatography in the same manner as in (2), and the solvent was distilled off with an evaporator. Next, fats and oils E were obtained by adding 0.02 parts of tocopherols (mixed tocopherols MDE-6000, manufactured by Yashi) to 100 parts of fats and oils obtained by mixing each fraction. The glyceride composition and fatty acid composition are shown in Table 1. Moreover, it was 1, 3-DAG / 1, 2-DAG = 2 (weight ratio) of fats and oils E.

(7) Preparation of Maintenance F

To 100 parts of fats and oils in which fats and oils and the rapeseed oil were mixed at a weight ratio of 1: 2, 0.02 parts of tocopherol (mixed tocopherol MDE-6000, manufactured by Yashi) and 4 parts of plant sterol fatty acid ester (manufactured by CardioAid-S, ADM) were added. , Maintenance F was obtained. The glyceride composition and fatty acid composition of fats and oils F are shown in Table 1. In addition, the constituent fatty acid composition of rapeseed oil is shown in Table 1 footnote (* 2).

(8) Preparation of fats and oils G and oils H

455 parts of reduced fatty acid by wintering soybean oil fatty acid, 195 parts of rapeseed oil fatty acid and 107 parts of glycerin were subjected to esterification using immobilized lipase (Lipozyme RM IM, Novozymes) (40 ° C., 5 hours). , 0.07 hPa). Subsequently, the immobilized lipase was separated by filtration, thin film distillation was performed, and then washed with water and deodorized. To 100 parts of this fat or oil, 0.02 parts of tocopherol (mixed tocopherol MDE-6000, manufactured by Yashi) was added. Here, what added 0.3 parts of plant sterols (phytosterol F, Tama Biochemical Co., Ltd.) was fats and oils G, and what added 4 parts was made fats and oils H. The glyceride composition and fatty acid composition of fats and oils G are shown in Table 1. Further, the 1,3-DAG content of the fat or oil G was 57.7%, and the 1,2-DAG content was 27.5%. Thus, 1,3-DAG / 1, 2-DAG = 2 (weight ratio).

(9) Preparation of fats and oils I-K and fats and oils L-N

The fats and oils A and G were mixed by the weight ratio 7: 3, 5: 5, 3: 7, and were set as the fats and oils I, J, and K, respectively. In addition, the fats and oils A and H were mixed by the weight ratio 7: 3, 5: 5, and 3: 7, and it was set as the fats and oils L, the fats, and the fats and oils N, respectively.

(10) maintenance 0, preparation of maintenance P

Seed oil, fats and oils A, and fats and oils G were mixed by the weight ratio 50:25:25, and fats and oils O were prepared. Moreover, the rapeseed oil, the fats and oils A, and the fats and oils H were mixed by the weight ratio 50:25:25, and the fats and oils P were prepared. In addition, rapeseed oil is the same as what was used for the said fats and oils F.

[Analysis method]

(i) glyceride distribution

10 mg of sample and 0.5 ml of trimethylsilylating agent ("silylating agent TH", manufactured by Kanto Chemical Co., Ltd.) were added to the glass sample bottle, which was heated and then heated at 70 ° C for 15 minutes. After addition of 1 ml of water, 2 ml of hexane was added and shaken well. After standing still, the hexane phase was extracted, subjected to gas chromatography (GLC), and analyzed.

GLC condition

Device ; Hewlett Packard Manufacture 6890 Type

column ; DB-1HT (manufactured by J & W Scientific) 7m

Column temperature; initial = 80 ° C, final = 340 ° C

Temperature rise rate = 10 ° C / min, held at 340 ° C for 20 minutes

Detector; FID, temperature = 350 ° C

Injection section; Split ratio = 50: 1, temperature = 320 ° C

Sample injection volume; 1㎛

Carrier gas; Helium, flow rate = 1.0 ml / min

(Ii) constituent fatty acid composition

To about 12 mg of the sample, 0.6 ml of a 1 / 2N sodium hydroxide methanol solution was added. Subsequently, after adding 0.6 ml of boron trifluoride methanol complex methanol products (made by Wako Pure Chemical Industries, Ltd.), it heated at 70 degreeC for 30 minutes. After addition of 1 mL of saturated saline solution, 1 mL of hexane was added, followed by shaking well. The hexane phase was extracted, anhydrous sodium sulfate was added, and the fatty acid methyl ester was prepared.

The methyl esterified fatty acid was provided to GLC for analysis.

GLC condition

Device ; Hewlett Packard Manufacture 6890 Type

Column: CP-Si188 for Fame (GE Sciences)

0.25mmm × 50m

Column temperature: initial = 150 ℃, final = 225 ℃

After holding at 150 ° C. for 5 minutes, the temperature was raised to 2 ° C./min and held at 225 ° C. for 15 minutes.

Detector; FID, temperature = 250 ° C

Injection section; Split ratio = 40: 1, temperature = 250 ° C

Sample injection volume; 1 μL

Carrier gas; Helium, flow rate = 1.0 ml / min

Table 1 Fatty acid composition in each fat or oil was handled as the same as the total fatty acid composition in all glycerides except fats and oils F.

Example 2 Preservation Test

Using the fats and oils A and B, the preservation test was done by the following method. 20 g of fats and oils were put into the glass sample bottle (50 mL volume), and it sealed with nitrogen, and was tight. This was stored in a freezer at -20 ° C. After 5 years, it was left to stand at room temperature, thawed, opened, and sensory evaluation was performed based on the following criteria for smell and appearance. The results are shown in Table 2.

smell

a: A deterioration smell and a chemical smell are hardly felt and are favorable.

b: The deterioration smell is slightly felt, but there is no chemical smell and is slightly good.

c: Deterioration smell and chemical smell, slightly bad.

d: Deterioration smell and chemical smell are strong and poor.

Exterior

a: The same liquid as a normal oil (salad oil), and is favorable.

b: Slightly higher viscosity than usual oil and slightly better.

c: There is a gel-like part, and it is slightly bad.

d: Gel-like part occupies most and is bad.

It was shown that the present invention has better odor and appearance than the comparative product, and good shelf life.

Example 3 Animal Experiment

With the composition shown in Table 3, the feed was prepared according to a conventional method. Six to seven week old Zucker rats were divided into four groups of six animals per group. First, preliminary breeding for 4 days with feed 1 (feeding schedule). Subsequently, each feed was used to raise for 9 days each. The feeding amount at this time was measured every day. On the last day of feed administration, dissection was performed, and the liver, perirenal adipose tissue, and pericardial adipose tissue were removed, and the weight thereof was measured. Moreover, the amount of triglycerides in soy sauce was measured. The results are shown in Table 4.

When the feed (feed 2) containing the present invention was administered, it became clear that the amount of triglycerides in the liver and the amount of tissues around the kidneys were lower than those of the comparative products (feeds 1, 3, 4). In addition, the total amount of feeding was significantly reduced, and it was shown that it had a feeding inhibitory effect.

Example 4 Preservation Test 1 at Low Temperature

What added 1%, 2%, and 4% of plant sterols (phytosterol F, Tama Biochemical Co., Ltd.) to fats and oils A was set as fats and oils Aa, fats, and oils Ac, respectively. Moreover, what added 1%, 2%, and 4% of plant sterol fatty acid esters (CardioAid-S, ADK) to fats and oils A was set as fats and oils Ad, fats Ae, and fats Af, respectively.

10 g of these fats and oils were put into the 20 ml volume glass sample bottle, the lid was closed, and it left still in the 5 degreeC and 10 degreeC thermostat. After 6 hours, the state of each sample after 24 hours was visually observed as the following evaluation criteria and evaluated. The evaluation results are shown in Table 5.

4 points | pieces: There is no precipitation or turbidity, and it is transparent and has fluidity.

3 points | pieces: There is a slight haze or precipitation, but there is fluidity.

2 points | pieces: There exists a precipitation in some parts and fluidity is impaired.

1 point: It solidifies and there is no fluidity at all.

By combining plant sterols (PS) and plant sterol fatty acid esters (PSE), it has been shown that the preservation at low temperatures of CLA-DAG is improved.

Example 5 Preservation Test 2 at Low Temperature

10 g of fats and oils A, fats and oils G, fats and oils I, K, fats and oils L and N, fats and oils O, and the fats and oils P were put into a 20 ml volumetric glass sample bottle, the lid was closed, and it left still in the thermostat at 5 degreeC and 10 degreeC. After 6 hours, each sample state after 24 hours was visually observed as the evaluation criteria similar to Example 4, and evaluation was performed. Table 6 shows the results of the evaluation. In addition, in Table 1, the whole constituent fatty acid composition of fats and oils A and G and the constituent fatty acid composition of DAG were handled similarly, and the weight ratio (CLA / PS) of the amount of CLA in DAG and the amount of PS in fats and oils was computed.

When the weight ratio (CLA / PS) of the amount of CLA in the DAG and the amount of PS in the fat or oil was less than 700, it was found that the shelf life at low temperature was improved.

Claims (5)

The following components (A) and (B): (A) Containing 15% by weight or more of diacylglycerol having an unsaturated fatty acid content of 80% by weight or more, a conjugated linoleic acid content of 2 to 92% by weight, and a ω3-based unsaturated fatty acid content of less than 15% by weight, and monoacylglycerol 100 parts by weight of a fat or oil having a content of 5% by weight or less and a free fatty acid content of 5% by weight or less and a weight ratio of 1,3-diacylglycerol / 1,2 diacylglycerol of 1 to 5 (B) 0.001 to 2 parts by weight of tocopherol A fat or oil composition containing the same. The method of claim 1, Furthermore, the fat or oil composition containing 0.05-30 weight part of (C) plant sterols. Food containing the oil-fat composition of Claim 1 or 2. A feed containing the fat or oil composition according to claim 1 or 2. A pharmaceutical product containing the fat or oil composition according to claim 1 or 2.